Sam had taken off across the country in the Impala leaving you and Dean stranded in Chicago. You don't know when he left, but when you woke up that morning all his stuff was gone along with Dean's beloved Baby.
You had spent the last half hour trying to calm down your boyfriend, and reassure him that his brother and his car would be ok. When he finally settled down he called up the telco company while typing away on your laptop trying to get Sam's GPS location. A few minutes later he hangs up and calls out for you. "He's in Tampa, Florida. We're gonna have to hot wire a car, start packing while I do that."
"You know how long it's gonna take to drive to Tampa? Why don't we fly, he's got Baby there so no point in having two cars anyway."
"Fly? No thanks. Who cares about having two cars, I'll just leave the other one in Tampa when I get my best girl back."
"Your best girl? I thought I was your best girl?" You stroll over to your and Dean's bed and take your laptop from Dean, searching for flights to Tampa. "There's a flight in two hours and we can get two seats next to each other. I'm gonna book it. Sam could go anywhere by the time we drive there, this way we have a better chance of catching up with him."
"I'm not flying, Y/N."
You can feel his body tensing beside you, so you put the laptop aside and crawl into your boyfriend's lap. You wrap your arms around his neck and peck his nose. "Ok, spill it, handsome. What's so bad about spending a few hours on a plane next to me?"
He sighs as he wraps his arms around your waist and hides his face in the crook of your neck.
"Come on, baby, use your words. Something's up and it's more than just Sam disappearing in your car." You kiss the top of his head and run your hands through his hair. When he continues to stay silent, you say, "wait! Are you scared of flying, baby? My big strong warrior is afraid of spending a few hours in a big metal bird?"
He sheepishly nods, his head still against your neck.
"It's ok, baby. I'll be right there beside you holding your hand the entire time. You can squeeze my hand and cuddle me as much as you want. We could even join the mile-high club if you want," you say with a smirk, even though he's not looking at you. After that comment though he places a kiss on your neck as he slowly pulls back.
"If that's on offer then I may have to overcome my fear."
"Does that mean I can book the flight and we can go get Sam and Baby back?"
He kisses you and nods his head reluctantly, you kiss him back before reaching behind you for your laptop to book the seats. Once your tickets are secured you kiss your boyfriend one last time before getting up to finish packing up and ordering a ride to the airport. When you are almost done Dean drops a heavy duffle on your bed. "What do you suppose you do with these, my frequent flier?"
"I have my contacts."
"You do realise this bag is full of knives, guns and various other weapons?"
"I know. Just trust me."
"Fine, but if we get kicked off the plane then just know that you will never get me in an airport again."
You saunter over to your panicking boyfriend hugging him tightly, "have a little faith in your girl, would ya, Winchester."
He just shakes his head and chuckles, kissing you as you hear a horn outside, "that'll be our ride, handsome." He pulls away and takes your hand in his, carrying his duffles over his other shoulder. He carefully loads your bags into the trunk of the black SUV you ordered, but when he comes back around the side of the car he catches you hugging the driver who is dressed in a flight attendant outfit. Dean clears his throat loudly causing you to pull away.
"Dean, this is my old hunting partner, Andre. Andre, this is my boyfriend Dean." You walk over to your boyfriend and reassuringly squeeze his hand. "Andre's a flight attendant now; he helps fellow hunters get around the country. So, yeah, I told ya I had it all under control."
Dean just nods, eyeing off the slightly shorter, leaner man. "Alright, that's quite enough overprotective jealousy from you," you say glaring up at your boyfriend, "Andre has a boyfriend. Speaking of how is Romeo?" you ask Andre.
"He's amazing as ever. I told him about hunting. It was rough after that but once I assured him I'm not in the big leagues anymore he calmed down. He still isn't exactly happy about me doing this part either though."
"He's just being protective. He loves you. This one can be the same at times," you squeeze Dean's hand again, smirking. "Now come on, we better get a move on before we miss our flight."
You hop in the back of the SUV with Dean as Andre jumps back in the driver's seat. You notice a smug smile on Dean's lips when you opt to sit with him instead of riding shotgun with your friend. Seeing this, you lean into him and whisper, "you really have nothing to worry about, I love you."
After not too long you pull up in the staff car park around the back of the airport. You and Dean take a duffle each and Andre takes your arsenal. Andre walks through the back entrance after pointing you in the direction of the passenger's check-in.
You make your way through check-in and security almost without a hitch, until Dean gets the secondary pat down thanks to his nervous demeanour. You poke fun at him, earning yourself a pat down as well. But thanks to Andre there's nothing on your bodies to find. The security guards let you go and grab your luggage to make your way to your gate. You still have 20 minutes to boarding so you stop by a cafe and get your caffeine fix and a sandwich for Dean, knowing his hanger would set in if he didn't eat soon. When you return to the gate with the coffee and sandwich he thanks you and offers you a bite of the sandwich which you happily take, before letting him finish the rest himself.
It's not long before you are boarding and getting comfortable in your allocated seats, you let Dean have the first choice. He opts for the aisle so he could get up and walk around if he needed to, which you are glad about because you wanted the window anyway, not that you planned to pay much attention to anything besides the handsome man beside you.
When the plane starts taxiing down the runway he grips your hand tight, while lowly humming a Metallica song. You squeeze back, reaching your other hand over to rest on his thigh. "I'm right here with you, baby. Just squeeze my hand."
The flight continues smoothly, Dean's hand never leaving yours. Eventually, you even rest your head on his shoulder, sporadically kissing his neck, to provide more comfort and distraction. Once the wheels are on the ground in Tampa he leans over and kisses your lips.
"Thank you for not making fun of me," he says against your lips.
"Hey, never. Everyone's scared of something, there's no use making you feel worse. Plus, you always do the same for me."
"I know I don't say it as much as I should but I love you, sweetheart."
"I understand why you don't. It's ok. You show me that you do every day. And anyway, I say it enough for the both of us."
Once the plane's completely stopped Dean stands up and grabs both of your bags from the overhead compartment, knowing you'd struggle to reach it. He takes both bags in one hand and your hand in the other, leading you out of the plane.
"It's officially over, you're back on solid ground," you say, squeezing your boyfriend's hand.
"Can we stick to driving from now on?"
"But how are you gonna take me to Bora Bora for our honeymoon then?" you joke.
"We'll take a ferry," he says matter-of-factly, not arguing with the suggestion of a marriage in the future. This makes your heart flutter.
You've always known that Dean isn't the type to ever walk away from the good fight, but you're okay with that, as long as keeps you by his side. You also know for all legal intents and purposes he is dead, but you figure that if you could be married by a certain angel it would mean so much more anyway. You haven't shared these hopes with Dean yet though, of course. It's not that you don't trust him, you just don't want to scare him off, plus you know he'd want to be the one to do the asking.
The second you're out of the airport gates you call Andre to get your bag back, Dean already calling Sam to get his car back. Unsurprisingly though, he doesn't get a response.
Andre meets you guys in the pickups section in another black SUV from the airport rental company. He drives you to the motel where Dean had last tracked Sam to. Dean lets out a deep sigh of relief when he sees Baby in one piece. Andre pulls up beside her and lets you both out.
"I hope I hear from you again soon, let me know when you and your Boo are gonna tie the knot. Dean and I will be the first on the guest list."
"For sure! The same goes for the two of you. Take care!" He drives off waving.
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